


A Game Dean Couldn't Lose

by thisisapaige



Series: Thisisapaige's Suptober20 Collection [14]
Category: Supernatural
Genre: Alternate Universe - Canon Divergence, Bisexual Dean Winchester, Castiel and Dean Winchester Use Their Words, Castiel and Dean Winchester in Love, Castiel in the Men of Letters Bunker (Supernatural), Castiel/Dean Winchester in the Men of Letters Bunker, Dean Winchester's Scooby-Doo Underwear, Demisexual Castiel (Supernatural), Emotional Sex, First Time, Fluff and Smut, Frottage, M/M, One Shot, Strip Poker, Suptober 2020 (Supernatural), They are so in love y'all, You heard it here first, that will be a tag one day
Language: English
Status: Completed
Published: 2020-10-15
Updated: 2020-10-15
Packaged: 2021-03-09 03:47:40
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,095
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27018304
Author URL: https://archiveofourown.org/users/thisisapaige/pseuds/thisisapaige
Summary: (For Suptober20. Day 14 Prompt: Fun & Games)⁂"I regret teaching you this game.""I didn't make the rules, Dean.""Well, neither did I!""No, but you did set the parameters. Shirt off, please."
Relationships: Castiel/Dean Winchester
Series: Thisisapaige's Suptober20 Collection [14]
Series URL: https://archiveofourown.org/series/1950343
Comments: 16
Kudos: 248





	A Game Dean Couldn't Lose

**Author's Note:**

> This was supposed to be a silly little piece about strip poker because I'm like 90% sure tomorrow's episode is gonna destroy me but _no._ Dean and Cas had to be all in love and stuff so they had to talk about _feelings_ and make this fic all about that.  
> This is set in some Cannon Divergence time between after the boys got the bunker and nowish. Dealer's choice on actually when. :)
> 
> Anyway, I only learned how to play poker today so---  
> (aaaand you're already off to find the steamy bits. Have fun! ;))
> 
> [This is my Tumblr. Sup?](https://thisisapaige.tumblr.com/)

"I regret teaching you this game."

"I didn't make the rules, Dean."

"Well, neither did I!"

"No, but you did set the parameters. Shirt off, please."

Dean sighed. When he salvaged (salvaged, Sam, not stole) the poker table from the side of the road for the Dean Cave and decided to test it out, he didn't expect this outcome. Cas was _good_ at poker. Since they were alone in the bunker for the next few days, and because Dean was a dumbass who doesn't know how to shut his mouth, he made a stupid joke before this whole thing started about playing strip poker. Cas paused, looked Dean over from head to toe, and with complete and utter seriousness, agreed. 

Well, Dean was too stubborn to back down and, okay, Dean probably imagined it, but Cas had this interesting (lustful? Yeah right, Dean) look in his eyes when he agreed. So, he and Cas sat down at the table and dealt the cards. The parameters Dean put in place was that the person who won a hand got to pick an article of clothing for the other player to remove. Dean spent his whole life playing poker. It was a game he couldn't lose. Dean expected to go a few rounds, expected to get Cas out of that damn trench coat, but, instead, Dean lost both his boots, one of his socks, his plaid overshirt, and his belt. Cas, on the other hand, was fully dressed.

This was not going as planned.

And now Dean had to take off his shirt.

"Not the sock?" Dean asked.

"I wouldn't want your foot to get cold," Cas said with a straight face. 

That straight face (or, uh, hopefully not too straight) was the thing that put Dean in this mess. One: it was distracting because Cas had a pretty nice face. And B: Cas had the uncanny ability to look bored and blank when he had a full house. 

Which was the reason Dean was about to lose his shirt.

"Isn't gambling a sin or something?" Dean asked.

"So is defying God, ending the Apocalypse, and cutting yourself off from Heaven." Cas shrugged. "Yet, here we are."

He had a point. Not long ago, Cas told the angels to fuck off (in a much more Cas-like way, of course) and moved into the bunker (for good this time; please for good this time). He was still an angel but he didn't have the juice for the big stuff anymore. Nowadays, Cas could smite a couple of demons, heal minor cuts and bruises, and confuse the ever-loving shit out of Dean.

Cas was around, like, all the time. Which was fantastic, don’t get Dean wrong (Cas finally stuck around), but it also made Dean’s life more complicated. 

Cas still had no concept of personal space. Every morning, Dean would wander into the kitchen for coffee. Every morning Cas would, without fail, show up a few seconds after Dean, slide right up to the counter and put his hand on Dean’s lower back when he grabbed an empty mug. Every morning, Dean let him. 

It wasn’t just that, though. It was everything: the little smiles when they passed each other in the hall, how Dean would catch Cas humming the song that played last in the Impala, and, Hell, even the looks Sam would get on his face when Dean and Cas stared at each other for too long. It was nice. It made the bunker feel like a home. 

Dean didn’t want to screw any of that up. He didn’t want to presume anything but, sometimes, Dean wondered. Actually, not just sometimes. All the time. All the fucking time, Dean wondered if Cas was doing it on purpose. Dean wondered if Cas knew how much his touch affected Dean, how it always had affected Dean. 

Because Dean was in love with Cas. It took a lot of work and a lot of soul searching for Dean to admit that to himself. He hadn’t told it to anyone else yet (he suspected Sam wouldn’t be surprised) and he wasn’t sure if he would. 

Cas was so new to life on Earth, so new to life in the bunker, so new to life with the Winchesters, that Dean tried so very, very, hard not to read too deeply into things. He didn’t succeed at that much. 

Dean couldn’t mess this up. He looked forward to Cas’s touch, looked forward to waking up, and there weren’t many times in his life he could say that. 

And then, Dean had to go and suggest strip poker. 

Why was he like this?

Cas was watching Dean from across the poker table, one eyebrow slightly raised, his chin raised just enough so that he could look at Dean through half-lidded eyes. It was a very commanding expression. One might say dominant. One might feel a little tingly at that idea.

One might say that it was Dean.

Dean stood from his chair because, hey, if he was going to do this he was going to make it a show. He stepped out from behind the table and turned his back to Cas. Dean wiggled his hips a little because, apparently, he had no self-control tonight (and there wasn't even any alcohol in his system to blame) then made the mistake of glancing over his shoulder. 

One elbow propped on the table, Cas rested his chin in his hand with his head tilted to the side. He licked his lips and Dean swore there was a glimmer in Cas’s eyes, a glimmer of that look he had when they started this whole thing. 

Taking a deep breath, Dean grabbed the hem of his shirt. Slowly, revealing his skin inch by inch, Dean pulled it over his head. 

He faced Cas and threw the shirt at him. “Happy now?”

Much to Dean’s annoyance, Cas caught the shirt. Much to Dean’s surprise, he smoothed it out and proceeded to fold it neatly. 

“Very,” Cas said.

Was it just Dean or was Cas’s voice even deeper than usual? Was it just Dean or was the way Cas handed Dean’s shirt kind of tender when he set it aside?

No, weird. It was just Dean. Had to be just Dean. 

Dean returned to his seat and gathered up the cards. He set them in front of Cas.

“Your deal,” Dean said. 

Dean's hand could go either way so he threw some chips into the pot. He was curious to see where things went. He was curious to see was Cas was going to do. He was curious to see if he was imagining Cas's distraction. 

It seemed like, every time Cas looked at Dean, he spent a little bit longer than necessary to place his bets. It seemed like Cas was a little too focused on Dean's skin and not enough on the game. 

The round ended. Dean won. Dean gleefully claimed his worthless chips, and couldn't help but laugh at how Cas's face fell. The former Angel of the Lord, current Angel of Free Will, was indeed pouting.

"Oh, Cas. I know." Dean smirked. "It's all fun and games until someone loses a…" He gave Cas an exaggerated once over, acting like this choice was a terrible burden. "Tie."

The tie. Really Dean? Had to go for that rhyming pun, huh?

Without a word of complaint or a raised eyebrow, Cas loosened his tie. He did it slowly, long fingers teasing the knot until it came loose, his eyes on Dean all the while. Once the tie was removed, Cas wound it around one hand. With the other, he released a few buttons on his shirt and…

Uh.

Uh, right, yeah. Poker. Dean won. So, time for a new hand. That was probably why Cas held the cards out to Dean, the tie folded on top of the stack. Dean accepted his prize in the form of one blue tie, adding it to his small, but not as small as it was a moment ago, pile of chips.

"So." Dean scratched his chest. Man, if it got any colder, Dean really would have perky nipples. "Have you given any more thought to what you're gonna do with your newfound freedom?"

"Playing poker has proven to be an enjoyable experience," Cas said. "That is if you deal."

"Oh, yeah. Right." Dean cleared his throat and distributed the cards. "But, I mean, there's gotta be something you wanna do, places you wanna go, things you want to experience." Dean's heart took on a rapid beat (please stay, please stay, please stay). "You can do anything you want. You don't have to hang out in the bunker. Y'know, if you don't want to."

"Who says I don't want to?" Cas threw a few chips into the pot.

"No! No, I'm not saying you--" Dean sighed. "I mean, you're really fine with this spending your days going on hunts with me and Sam then coming back to the bunker where I force you to watch a bunch of movies?"

"I am."

"Oh. Oh, that--" Dean's heart sang (he wants to stay, he wants to stay) but it also thumped worriedly (but what if he leaves again?)."That's, uh, cool. Because we're totally watching Tombstone again tomorrow."

Cas hummed. "I'm looking forward to it."

Dean traded three cards from his hand. Much better. Things were looking up for him. "But, for real, are there things you want to do? Things you want to experience differently than before? Maybe for the first time?"

Cas stared at his cards, quiet for a long moment. "A few things, maybe." He raised his eyes to look at Dean. Cas's eyes roamed, tracing every line of Dean's body. A pleasant shiver ran up Dean's spine. Cas continued, "Things I never wanted before. Things I didn't know I could experience."

The click which sounded when Dean swallowed had to be audible from the next room. "Like what?" 

"Like…" Cas held Dean's gaze and there it was. There it was: that look in Cas's eyes that got Dean into this whole mess to begin with. "Like--" Cas licked his lips. Dean categorized every movement with rapt attention. "Like baking a pie. I've never done that before. There are so many _flavours_ I haven't tried."

Was it just Dean, or did Cas empathize the word flavours a little too much?

"Uh, yeah sure. I can teach you that." Dean broke away from Cas's stare and fiddled with the nearest pile of chips. They rattled in Dean's hand. "But don't they, like, all taste like molecules to you?"

"Yes, but different molecules. Sometimes their varied compositions can be interesting." Cas raised. "I think I'd like to try something complex, yet simple at the same time."

Dean couldn't remember what cards he had. He threw his chips into the pot anyway. "Maybe lemon meringue? I mean, meringue seems simple until you're making it and, uh, the lemon is sweet and sour. So it's like, um, the best of both worlds." 

Best of both worlds? C'mon Dean (too obvious) that was a bit much. Then again, people didn't often pick up on those kinds of things unless they were already in the know. Dean wouldn't expect Cas to pick up on that kind of hint (not obvious enough?) with the fact that he wasn't in the know. Maybe.

Because, after all, there was the distinct possibility Cas really was just talking about pie.

"Best of both worlds," Cas echoed. He absorbed the words, a small soft smile crossing his face. "Yes. I think I like that."

Wasn't Dean supposed to be doing something? It was hard to recall when he was busy admiring how such a tiny smile could light up the entire room. Dean looked down at his hands. Oh. Right. Cards. Poker.

Strip poker.

"Shall we see who won?" Cas asked.

Dean again. This time, he was smart enough to ask for the trench coat. He wasn't, however, smart enough to prepare himself for the sight of a trench coatless Castiel, Angel of a Hot Body. Speechless, Dean took the trench coat, still warm from Cas's body heat, as his newest prize and hung it on the back of his chair. Dean totally did not have to resist the urge to bury his nose in it and breathe in that fresh rain and ozone smell (something so distinctly Cas that every stormy day reminded Dean of him) coming off of it. 

Because that would be absurd.

Castiel, Angel of No Trench Coat, might have been hot but Castiel, Angel of No Suit Jacket and Only a White Button Down Shirt, burned through the chart. Er, whatever chart Dean was using for this metaphor.

Forearms.

For the first time in Dean's life, he understood the forearm thing. Once Cas had surrendered the suit jacket to Dean, he rolled his sleeves up to the elbow, the action smooth and natural. Cas practically swam in that trench coat so Dean never got to appreciate the fact that Cas was actually pretty buff and had nice, smooth, tan skin that just looked so very… touchable. 

Cas never seemed touchable before. He was always so angelic, always full of immeasurable power, always on a different, higher level than Dean, the lowly human. But, over the last few years and especially over the time since he moved into the bunker, Cas just seemed like a guy. Like Cas. Like someone who wanted to try baking pies (it was about pies, right?). Like someone Dean could sit beside and drink his morning coffee with in peace. Like someone Dean could love.

Dean knew he was flying too close to the sun here, but he wanted to see more of Cas, all of Cas, the man, the angel, the individual person sitting there at a salvaged poker table in the Dean Cave. All of Cas. 

So, of course, Dean lost the next hand.

"Pants, please," Cas said. 

That was it. No hesitation. No preamble. Just, "Hey, Dean, wanna strip for Cas?"

And yeah. Yeah. He kind of did. 

But, uh, Dean forgot he put on the Scooby-Doo boxers that morning.

"Um, uh, er," Dean stuttered. "It's laundry day?" 

Shimmying out of his pants? A-okay! Getting caught wearing his favourite lucky boxers? Not so much.

"Of course, Dean," Cas said, his grave nod failing to hide his amusement. "Laundry day."

The silver lining in the ridiculousness that had become Dean's life was that he finally made Cas smile wide enough that the corners of his eyes crinkled. A Cas with happy eye crinkles was a beautiful sight indeed. That made everything worth it. 

Good thing Cas let Dean keep that one sock. Otherwise, Dean might've found it cold having no pants and all.

"What other underwear do you have in your collection?" Cas asked, for all the world like it was an innocent question.

That made Dean flush. "That's for me to know and you to find out."

Cas hummed, low and contemplative. "I hope I do."

"Cas, you--" Dean blush travelled down his chest. There was no way to hide it, considering his state of undress. "You don't know what you’re say--"

"I know exactly what I am saying, Dean." Cas took a deep, stabilizing breath (what a human gesture) and asked, "Do you wish to continue this game?"

Dean knew, without a doubt, Cas wasn't referring to poker.

"But, that's the thing, right?" Dean bit his bottom lip, staring down at the tabletop. "Once the game is over, it’s over.”

“Games are played to be--” Cas paused. Dean couldn’t look at Cas, couldn’t face any kind of rejection, so when Cas reached across the table to touch Dean’s hand, Dean was astonished by the gentleness of it. “Can we drop the metaphors now?”

When Cas pulled his hand away, Dean had a moment of insanity when he thought about grabbing it before Cas could leave. Dean didn’t do that, nor did he raise his head, but he did nod for Cas to go on.

“I want to be here,” Cas said. “With you.”

Dean’s heart stopped (with Dean?) and started back up with a vengeance, hammering so hard against his chest he worried it would burst out of him like in a Looney Tunes cartoon. He couldn’t believe it. He couldn’t. 

“Well, yeah,” Dean said, “I don’t blame you for getting away from the angels. So, I guess you would wanna be with the huma--”

“You’re not listening, Dean,” Cas said, stern but kind. He spoke the next part carefully, plainly. “I want to be here. _With you._ ”

“Why?” Dean raised a hand, knowing Cas was about to launch into another affirmation, even without looking at him. “Hear me out. There’s a whole big wide world out there. There’s way more you could do than sit in this underground bunker and chase monsters every day. You’re a free angel, Cas. You have all these places you could go and--” Dean groaned because he couldn’t find the words, because he was sitting in his boxers and it was a really strange time to have a deep heartfelt conversation, because he loved Cas and it scared the absolute shit out of him. “My job sucks. I’m kind of a dick. This ain’t exactly country living. I wouldn’t wish this life on anyone. And you’re-- you’re you. I’m just a guy. You’re gonna get bored of this sooner or later and the last thing I want is for you to be miserable.” 

“You’re not _just_ anything, Dean.” Cas’s soft tones made Dean finally raise his gaze. Cas’s (blue and easy to get lost in) eyes were just as soft as his tone. “And this isn’t boring. There’s not much opportunity to play strip poker in Heaven.” Cas smiled. Dean found himself smiling back. “I know what miserable feels like, Dean, and it feels like being up there, in Heaven, away from those I care about. Away from you.” Cas gestured from Dean to himself. “But this? I think this is what one calls happiness.”

A giggle bubbled up in Dean’s throat because this was so, so ridiculous. He was about thirty seconds away from crying in his Scooby-Doo underwear because the angel he’d been in love with for years just said that being with Dean made him happy. Dean hid his face in his hands and tried to accept what Cas was saying, tried to accept his love. 

Well, this whole thing started with a silly game, so Dean figured he should end with one. Dean reached for the cards.

“One last game.” Dean stared at Cas, making sure he was understood. “Winner takes all.”

Cas held that gaze for a few moments then, all at once, it became clear he understood Dean’s meaning. “Winner takes all.”

They didn’t bother with the chips. Once the cards were dealt, they turned them over. Dean’s was a mix of suits, two pair of kings and nothing else worthwhile. Cas, however, was all hearts, ace through ten. 

“You win,” Dean said, his voice dry.

“I win,” Cas said. He didn’t move. He only watched Dean. “We don’t have to do anything you don’t want to do, Dean.”

“Oh, I want to.” Dean sat up in his chair, running his hand down his chest. He liked how Cas tracked the movement, how his mouth opened just a tiny bit, how his pink tongue was caught between his lips. “I’ve wanted to for a long time. What about you?”

“Maybe not for as long,” Cas said (oh, yeah, his voice was definitely deeper), “but I want to. Very much.”

Dean stood from the table and offered a hand to Cas. “Then follow me.”

Cas took Dean’s hand, allowing himself to be pulled out of his seat and into the bunker’s hallways. Dean led them both to his bedroom because, if they were going to do this, they were going to do this properly. 

When the door closed behind them, Cas already had Dean pressed up against the wall. Cas kissed him passionately, eagerly, like Dean was something precious, something needed, something worthy of worship. Hungry hands trailed down Dean’s chest, sending shivers down his body and heat to pool in his core. Dean gasped when Cas’s tongue teased the sensitive skin of his neck and groaned when Cas’s hands slid under his boxers to cup his ass.

Dean was not expecting Cas, an angel he was pretty sure had little to no experience at this kind of thing, to be so damn _good at it_.

“Where--” Dean sighed in contentment as Cas trailed kisses down his chest. “Where did you learn this?”

Cas chuckled, a sinful sound. “I watched humanity for many years, Dean. I never understood the need for _this_ ”-- Cas rolled his hips, both he and Dean groaning at the friction-- “until I knew you. Then I had all these thoughts, these daydreams--” 

Dean grabbed at Cas’s hips, trying to hold him there, trying to keep him close. “Daydreams?”

“ _Sinful_ ones,” Cas purred into Dean’s ear and damn if that didn’t light a fire, like, everywhere in Dean’s body. “Believe me, I was only a few mornings from taking you against the kitchen counter.”

“Oh,” Dean breathed. So, those touches did mean something. “You still could.”

“Oh, I will.” Cas curled his fingers in the waistband of Dean’s underwear. “But I believe we should focus on the task at hand.”

They went from the wall to the bed so quickly, Dean wouldn’t be surprised if Cas used his wings. Dean landed on his back and Cas braced himself on top of Dean. Cas's hands touched everywhere; his mouth kissed everything. Though he tried desperately to pry open the buttons on Cas’s shirt, Dean couldn’t make his fingers cooperate. Cas’s hands and mouth had Dean undone, unable to do anything but revel in his angel’s touch.

At some point, Dean got naked. Well, naked except for that one sock. Cas left it on purpose, Dean bet. What was maddening was that Cas still wore that damn shirt, those shoes and, worst of all, his pants.

“Cas.” Dean was wrecked. God, he was wrecked but he needed more. He needed all of Cas. “Cas, please, need you.” He tugged at Cas’s belt. 

Cas kissed Dean’s lips once, twice, then sat up, straddling Dean’s hips. Dean, his breaths hard and heavy, propped an arm under his head so he could better view the show. Cas’s deft fingers worked the buttons open on his shirt then proceeded to unbuckle his belt. A metallic clash signalled the loss of the belt. Neither jumped at the sound or cared where it landed. They only had eyes for each other. 

Skin. Miles upon miles of tanned skin and toned muscles descended upon Dean and Dean made it his mission to touch every single part. Cas, every last bit of him laid bare, pressed against Dean, skin to skin, mouth to mouth. They moved together, gasping, moaning, breathing each other in, watching each other come apart at the seams.

Dean gripped Cas’s shoulders, dug his heels into the back of Cas’s thighs, trying desperately to get closer, closer, closer, to him. Dean needed more. He needed _more._ He needed more of Cas. He needed all of Cas. 

Cas reached in between their bodies, fitting both their cocks into his hand. God, Cas had big hands. Cas stroked them both, building, building, building the tension within them. Dean bucked up into Cas’s hand, matching the increasingly frantic rhythm. 

Closer. Closer Closer.

It happened all at once. Dean cried out Cas’s name as the only warning he could give, then allowed his pleasure to overtake him. Cas kept moving, kept giving Dean everything, and Dean reached a height he didn’t know was possible. Somehow, he went higher still when Cas choked out Dean’s name as he reached his peak. 

If that was how it felt with just hands, Dean couldn’t wait to figure out what else they could do.

A few moments later, Dean lay under the covers, all cleaned up by Cas’s extremely handy angel skills, wholly satisfied. Cas joined Dean, offering his arms as a place to rest. Dean went into them willingly. 

“You know,” Cas said, carding his fingers through Dean’s hair, “I think you cheated on that last hand.”

“But I lost,” Dean muttered into Cas’s chest.

“No, you didn’t. We both won.”

Dean smiled against Cas’s skin. “Yeah, I guess you’re right.” 

Poker really was a game Dean couldn’t lose. 


End file.
